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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2020-03-16 16:00:04 UTC
Update Date2020-06-03 15:12:17 UTC
HMDB IDHMDB0240641
Secondary Accession NumbersNone
Metabolite Identification
Common NameAscorbic acid 3-sulfate
DescriptionAscorbic acid 3-sulfate belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Ascorbic acid 3-sulfate is a metabolite of vitamin C. Vitamin C, also known as L-ascorbic acid or L-ascorbate, is an essential nutrient for humans and certain other animal species. In living organisms, ascorbate acts as an antioxidant by protecting the body against oxidative stress. It is also a cofactor in at least eight enzymatic reactions including several collagen synthesis reactions that, when dysfunctional, cause the most severe symptoms of scurvy (Wikipedia). Ascorbic acid 3-sulfate has been identified in urine (PMID: 5572173 ).
Structure
Data?1584374519
Synonyms
ValueSource
L-Ascorbate 3-sulfateGenerator
L-Ascorbate 3-sulphateGenerator
L-Ascorbic acid 3-sulfuric acidGenerator
L-Ascorbic acid 3-sulphuric acidGenerator
Ascorbic acid 3-sulfateHMDB
Ascorbic acid 3-sulphateHMDB
L-Ascorbic acid 3-sulfateHMDB
L-Ascorbic acid 3-sulphateHMDB
L-Ascorbic acid-3-sulfuric acid esterHMDB
L-Ascorbic acid-3-sulphuric acid esterHMDB
Chemical FormulaC6H8O9S
Average Molecular Weight256.18
Monoisotopic Molecular Weight255.988903012
IUPAC Name[(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]oxidanesulfonic acid
Traditional Name[(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2H-furan-3-yl]oxidanesulfonic acid
CAS Registry Number22430-27-9
SMILES
[H][C@@]1(OC(=O)C(O)=C1OS(O)(=O)=O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H8O9S/c7-1-2(8)4-5(15-16(11,12)13)3(9)6(10)14-4/h2,4,7-9H,1H2,(H,11,12,13)/t2-,4+/m0/s1
InChI KeyFBFZPSQPKNIVMT-ZAFYKAAXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Organic sulfuric acid or derivatives
  • 1,2-diol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-4.4ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability20.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedMaleScurvy details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9600241
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11425365
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Baker EM 3rd, Hammer DC, March SC, Tolbert BM, Canham JE: Ascorbate sulfate: a urinary metabolite of ascorbic acid in man. Science. 1971 Aug 27;173(3999):826-7. doi: 10.1126/science.173.3999.826. [PubMed:5572173 ]